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Jamaica Vacations

Pack those stellar shades. We have Jamaica vacation deals for you!

If there’s one thing you should spend in this busy world, it’s your vacation days. We know it’s easy to hang onto them, but Hotwire votes for putting them to use. It’s time to let an adventure lead you away from the daily grind. Stock up on what really matters on your trip to Jamaica – great memories and a tall tale or two.

Hotwire can help you find your travel bliss with Jamaica vacation packages. Bundling your hotel, car and flight means more unexpected fun with the money you saved. We’ll cover the bases; now it’s time for you to get up and go!

Pack everything you want – then take half of it out

We mean it. It’s far too easy to over-pack. We recommend picking your essentials and washing them along the way. Then you’ll have room for that goofy souvenir you know you want – or for some new outfits from that cute boutique you discover.

Bring comfortable walking shoes on your trip to Jamaica

No one should have to endure walking tours in dress shoes or high heels. No one.

Bring photocopies of your passport or license

You flew home from a great Jamaica vacation but your most important documents stayed behind. We’ve heard that story before and recommend keeping an extra copy on hand – just in case. Hey, at least it wasn’t a family member.

Don’t underestimate the power of earplugs

Among crying babies, rowdy crowds and honking horns, take our word for it. One pair can save you from the zombie-like state of a sleepless night.

Always carry some cash

You’ll be ready for anything from an evil ATM to lost credit cards. Holding a little extra cash in your wallet and carry-on means you can breathe easy if anything unexpected pops up.

Explore like a local

Guidebooks and maps are great for getting an overview of the place, but to really dig in, go where the locals go. Pick up a newspaper or city magazine to see what restaurants and neighborhoods are hot. Check events listings and go see a band or attend a street festival. Or ask your friends for recommendations. You’d be surprised who in your circle knows Jamaica well.

Top Hotel Deals

See all 312 Hotels in Jamaica
Cold Moon Farm Bed and Breakfast

Cold Moon Farm Bed and Breakfast

251 Pratt Bridge Road, Jamaica
    2.5 out of 5.0
     
     

    Situated in Jamaica, this bed & breakfast is within 6 mi (10 km) of Ball Mountain Dam, Ball Mountain State Park, and Jamaica State Park. Stratton Mountain Golf ...

    Three Mountain Inn

    Three Mountain Inn

    3732 Vermont Routes 100 and 30, Jamaica
      3.5 out of 5.0
       
       

      Situated in a state park, this inn is 0.9 mi (1.4 km) from Jamaica State Park and within 6 mi (10 km) of Ball Mountain Dam and Ball Mountain State Park. Stratton ...

      Immaculate - Stratton, Mount Snow

      Immaculate - Stratton, Mount Snow

      98 Gleason Farm Lane, Jamaica
        3.5 out of 5.0
         
         
        Colonial Motel And Spa

        Colonial Motel And Spa

        889 Putney Rd, Brattleboro
          3.0 out of 5.0
           
           

          Located in the heart of Brattleboro, this motel is 0.7 mi (1.1 km) from United States Navy Seabee Bridge and within 3 mi (5 km) of Brattleboro Common and Brattleboro ...

          Colonial Motel And Spa$69

          Colonial Motel And Spa$69
          Palmer House Resort

          Palmer House Resort

          5383 Main St, Manchester Center
            3.0 out of 5.0
             
             

            Located in the heart of Manchester Center, this golf hotel is within a 15-minute walk of Gander Gallery and Manchester Designer Outlets. Dana L. Thompson Memorial ...

            Palmer House Resort$98

            Palmer House Resort$98
            Hampton Inn and Suites Manchester

            Hampton Inn and Suites Manchester

            4519 Main St, Manchester
              2.5 out of 5.0
               
               

              Situated in the city center, this hotel is close to Manchester Designer Outlets, Orvis Fly Fishing, and American Museum of Fly Fishing. Also nearby are Southern ...

              Hampton Inn and Suites Manchester$128

              Hampton Inn and Suites Manchester$128
              Hampton Inn Brattleboro

              Hampton Inn Brattleboro

              1378 Putney Road, Brattleboro
                2.5 out of 5.0
                 
                 

                Situated in Brattleboro, this hotel is 0.7 mi (1.2 km) from United States Navy Seabee Bridge and within 3 mi (5 km) of Brattleboro Common and Brattleboro Museum ...

                Hampton Inn Brattleboro$107

                Hampton Inn Brattleboro$107
                Holiday Inn Express Springfield

                Holiday Inn Express Springfield

                818 Charlestown Rd, Springfield
                  2.5 out of 5.0
                   
                   

                  Situated in a rural location, this hotel is within a 15-minute walk of Baltimore Covered Bridge and Eureka Schoolhouse. The Fort at No.4 Open Air Museum is 1.3 ...

                  Holiday Inn Express Springfield$110

                  Holiday Inn Express Springfield$110
                  Mount Snow Condominiums

                  Mount Snow Condominiums

                  89 Grand Summit Way, West Dover
                    3.5 out of 5.0
                     
                     

                    Conveniently located near the ski slopes, this West Dover condo building is 0.2 mi (0.4 km) from Mount Snow and within 16 mi (25 km) of Mount Snow Golf Course ...

                    Inns at the Equinox

                    Inns at the Equinox

                    3567 Main Street Route 7A, Manchester
                      3.0 out of 5.0
                       
                       

                      Situated in Manchester, this spa hotel is within a 10-minute walk of American Museum of Fly Fishing and Orvis Fly Fishing. Southern Vermont Arts Center and Equinox ...

                      Inns at the Equinox$130

                      Inns at the Equinox$130

                      Top Flight Deals

                      Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.